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Cheap flights from Chicago Midway Airport to Milan from $339

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
KLM Logo
10:43 am - 9:25 am
MDW
-
MXP
15h 42m
1 stop
KLM Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$977KLM
Tue, Apr 14 - Tue, Apr 21
Delta Logo
12:53 pm - 12:05 pm
MDW
-
MXP
16h 12m
2 stops
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$981Delta
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:45 am - 9:20 pm
MDW
-
MXP
30h 35m
2 stops
Multiple Airlines Logo
7:00 am - 6:35 pm
MXP
-
MDW
18h 35m
2 stops
$1,066Multiple Airlines
Tue, Jun 2 - Mon, Jun 8
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$1,071KLM
Mon, Mar 16 - Tue, Mar 31
Multiple Airlines Logo
11:00 am - 6:15 pm
MDW
-
LIN
25h 15m
3 stops
Multiple Airlines Logo
2:30 pm - 10:05 am
LIN
-
MDW
26h 35m
3 stops
$1,080Multiple Airlines
Fri, Mar 27 - Sun, Apr 5
KLM Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
KLM Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$1,081KLM
Wed, Mar 18 - Wed, Apr 15
Delta Logo
10:49 am - 9:45 am
MDW
-
MXP
15h 56m
2 stops
Delta Logo
11:00 am - 10:31 pm
MXP
-
MDW
17h 31m
2 stops
$1,085Delta
Wed, Mar 4 - Wed, Mar 11
Delta Logo
1:29 pm - 10:35 am
MDW
-
MXP
14h 06m
2 stops
Delta Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m
1 stop
$1,086Delta
Mon, Mar 2 - Wed, Mar 18
KLM Logo
12:47 pm - 9:25 am
MDW
-
MXP
13h 38m
1 stop
KLM Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$1,087KLM
Fri, Apr 10 - Sat, Apr 18
Delta Logo
12:53 pm - 12:05 pm
MDW
-
MXP
16h 12m
2 stops
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$1,091Delta
Fri, Apr 17 - Sat, Apr 25

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets
KLM
Apr 14
MDW10:43 amChicago Midway
15h 42m
1 stop
MXP9:25 amMilan Malpensa
Apr 21
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$977
KLM
Mar 16
MDW10:45 amChicago Midway
15h 20m
1 stop
MXP8:05 amMilan Malpensa
Mar 31
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$1,071
KLM
Mar 18
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP8:05 amMilan Malpensa
Apr 15
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$1,081

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets
Delta
Apr 14
MDW12:53 pmChicago Midway
16h 12m
2 stops
MXP12:05 pmMilan Malpensa
Apr 21
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$981
Delta
Mar 4
MDW10:49 amChicago Midway
15h 56m
2 stops
MXP9:45 amMilan Malpensa
Mar 11
MXP11:00 amMilan Malpensa
17h 31m
2 stops
MDW10:31 pmChicago Midway
$1,085
Delta
Mar 2
MDW9:34 amChicago Midway
16h 31m
2 stops
MXP9:05 amMilan Malpensa
Mar 18
MXP11:00 amMilan Malpensa
17h 31m
2 stops
MDW10:31 pmChicago Midway
$1,086

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Milan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 4/14

10:43 am-9:25 am

1 stop15h 42m

Milan Malpensa

Tue 4/21

11:40 am-10:28 pm

1 stop17h 48m

$977

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 4/14

12:53 pm-12:05 pm

2 stops16h 12m

Milan Malpensa

Tue 4/21

11:40 am-10:28 pm

1 stop17h 48m

$981

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 6/2

7:45 am-9:20 pm

2 stops30h 35m

Milan Malpensa

Mon 6/8

7:00 am-6:35 pm

2 stops18h 35m

$1,066

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/16

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$1,071

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Fri 3/27

11:00 am-6:15 pm

3 stops25h 15m

Milan Linate

Sun 4/5

2:30 pm-10:05 am

3 stops26h 35m

$1,080

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/18

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Wed 4/15

11:40 am-10:28 pm

1 stop17h 48m

$1,081

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/4

10:49 am-9:45 am

2 stops15h 56m

Milan Malpensa

Wed 3/11

11:00 am-10:31 pm

2 stops17h 31m

$1,085

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/2

1:29 pm-10:35 am

2 stops14h 06m

Milan Malpensa

Wed 3/18

10:05 am-10:31 pm

1 stop18h 26m

$1,086

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 4/10

12:47 pm-9:25 am

1 stop13h 38m

Milan Malpensa

Sat 4/18

11:40 am-10:28 pm

1 stop17h 48m

$1,087

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 4/17

12:53 pm-12:05 pm

2 stops16h 12m

Milan Malpensa

Sat 4/25

11:40 am-10:28 pm

1 stop17h 48m

$1,091

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,197. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,462.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

13h 18m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan takes 13h 18m
There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.
Search flight deals

  • How far is Chicago Midway to Milan by plane?

    Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 13h 18m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milan?

    Prices for flights from Chicago Midway Airport to Milan are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milan?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

  • What documentation or ID do you need to fly to Milan?

    The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Brescia
Stresa
Levanto
Livigno
Monza
Assago
Bellano
Domodossola
Lecco
Crema
Rho
Cernobbio
Moltrasio
Saronno
Bormio
Baveno
Asti

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport